HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Methyl 2-methoxy-4-(phenylethynyl)nicotinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 4-iodo-2-methoxynicotinate | HCID 58819970 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Product | Methyl 2-methoxy-4-(phenylethynyl)nicotinate | HCID 58093657 | — |
Reaction Steps
A mixture of methyl 4-iodo-2-methoxynicotinate (400 mg, 1.36 mmol), ethynylbenzene (167 mg, 1.63 mmol), Pd(PPh3)2Cl2 (47 mg, 0.068 mmol), CuI (7.7 mg, 0.04 mmol) and triethylamine (400 uL) is stirred at room temperature for 20 hours. The mixture is diluted with water, made alkaline with K2CO3 and extracted with CHCl3. The organic layer is washed with brine, water and concentrated under vacuum. The title compound is purified by silica gel column chromatography using hexane/ethyl acetate as eluent. MS m/z 268.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546370B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-7cb4d83a9beb4015a4ac07bb86425a80 |
| Source note | uspto-grants-2013_10 |